Radiation cured (typically free radical UV light photopolymerization) coatings and inks are widely used in the coatings and printing industry. Radiation cured coating and ink formulations based cyclohexanedimethanol diacrylates provide excellent end-use properties for the cured coating (such as hardness and strength) but such formulations are difficult to use because the cyclohexanedimethanol diacrylates are solid materials at room temperature and are insoluble in most acrylates. Liquid coating and ink formulations based on ethoxylated or propoxylated cyclohexanedimethanol diacrylates are known but the resulting coating has poorer end use properties.
For example, 1,4-cyclohexanedimethanol has been alkoxylated with either ethylene oxide or propylene oxide and then acrylated to form alkoxylated cyclohexanedimethanol diacrylate based compounds in Scheme 1.

These products are readily soluble in the acrylates typically used in UV curable formulations and available from Sartomer Company and from Kowa American Corporation as liquids at room temperature. However, the alkoxylation of the 1,4-cyclohexanedimethanol leads to product mixtures with significantly enlarged molecular weights, i.e., m and n are both significantly larger than 1 and represent a statistical mixture. This leads to an undesirable increase in the specific molecular weights of these monomers (ratio of MW to the number of reactive functional groups); thus, the monomer contains a relatively small proportion of functional groups. In addition, the alkoxylation reaction generates useless byproducts such as nonionic, high molecular weight water-soluble poly (ethylene oxide) polymers and 1,4-dioxane. Furthermore, UV cured coatings made from these monomers have inferior properties.
Other related cyclohexanedimethanol based compounds include those disclosed in U.S. Pat. No. 7,943,725, which is owned by The Dow Chemical Company. The U.S. Pat. No. 7,943,725 patent discloses liquid acrylate based compounds of Scheme 2 (below),

These diacrylate compounds exist as a mixture containing the 1,3- and 1,4-isomers in an approximately 1-to-1 ratio. A disadvantage of this mixture is that it is a mixture of predominantly solid (but also some liquid) at room temperature, whereas liquid compounds are preferred. In order to generate the desired mixture of liquid diacrylates, it is necessary to either reduce the amount of the trans-1,4-cyclohexanedimethanol isomer in the starting diol to below 15% or purify the diacrylate reaction mixture by reducing the trans-1,4-diacrylate content to below 15%. These purifications are time consuming and lead to increased costs associated with the preparation of the monomer mixture.
It would be advantageous if liquid cyclohexanedimethanol diacrylate based coatings and ink formulations having improved properties, and that 1) did not create a statistical mixture of products, 2) reduced the formation of by-products, and 3) did not require a separate purification step to remove the trans-1,4-cyclohexanedimethanol isomer, could be prepared.